Diethyl Ether → 3-Bromo-5-tert-butyl-6-hydroxy-2-methyl-benzaldehyde

HRID 1765855

反応式

HRID 1765855 の反応式
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1.[CH2:14]([O:16]CC)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([C:5]([OH:9])=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1)[CH:14]=[O:16]

参加物

5

反応物 2

HCID 3283Diethyl EtherHCID 187986984-Bromo-2-(tert-butyl)-5-methylphenol2 回

生成物 1

HCID 211071503-Bromo-5-tert-butyl-6-hydroxy-2-methyl-benzaldehyde収率 61%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

実験手順

A stirred, cooled (ice bath) solution of 4-bromo-2-tert-butyl-5-methyl-phenol (Intermediate 139, 0.85 g, 3.5 mmol) in anhydrous dichloromethane (7 mL) was treated with titanium tetrachloride (0.64 mL, 5.8 mmol) followed by α,α-dichloro methyl ether (0.3 g, 3.5 mmol). The reaction mixture was allowed to warm to ambient temperature for 4 h. The reaction mixture was diluted with diethyl ether, washed with brine (×1) and dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue which was subjected to flash column chromatography over silica gel (230–400 mesh) using 1% ethyl acetate in hexane to afford the title compound as a yellow solid (0.58 g, 61%).

後処理

  1. washwashed with brine (×1)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo to a residue which

出典と根拠

ORDレコード
ord-4d4f1513ee864168b68e8f9d309f3b12
出典データセット
uspto-grants-2007_06
特許番号
US07226951B2

関連ノート

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